ArticleACS catalysis2019
Retooling Asymmetric Conjugate Additions for Sterically Demanding Substrates with an Iterative Data-Driven Approach.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 49 citations in OpenAlex.
- Chiral Analysis for High-Throughput Reaction Screening: Recent Advances in Accelerating Asymmetric Catalysis Discovery.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Elucidating Ligand-Dependent Selectivities in Pd-Catalyzed C-H Activations.Angewandte Chemie (International ed. in English) · 2025Article
- Challenges in Mechanistic Investigation of a Flexible Aminocatalyst as Demonstrated through Enamine Formation.ChemistryOpen · 2025Article
- Mathematical Framework to Identify Optimal Molecule Based on Virtual Ligand Strategy.Journal of chemical information and modeling · 2025Article
- Asymmetric alkyl-alkyl coupling between electron-deficient and unactivated alkenes to access α-chiral phosphines by Ni catalysis.Science advances · 2025Article
- Computational tools for the prediction of site- and regioselectivity of organic reactions.Chemical science · 2025Review
- Article
- An efficient and flexible approach for local distortion: distortion distribution analysis enabled by fragmentation.Chemical science · 2025Article
- Rapid prediction of conformationally-dependent DFT-level descriptors using graph neural networks for carboxylic acids and alkyl amines.Digital discovery · 2025Article
- Reaction-Agnostic Featurization of Bidentate Ligands for Bayesian Ridge Regression of Enantioselectivity.ACS catalysis · 2024Article
- Aromatic-Carbonyl Interactions as an Emerging Type of Non-Covalent Interactions.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Benchmarking machine-readable vectors of chemical reactions on computed activation barriers.Digital discovery · 2024Article
- A genetic optimization strategy with generality in asymmetric organocatalysis as a primary target.Chemical science · 2024Article
- Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis.Beilstein journal of organic chemistry · 2024Review
- Computer vision as a new paradigm for monitoring of solution and solid phase peptide synthesis.Chemical science · 2023Article
- Structure-Reactivity-Property Relationships in Covalent Adaptable Networks.Journal of the American Chemical Society · 2022Review
- Fluorine in metal-catalyzed asymmetric transformations: the lightest halogen causing a massive effect.Chemical science · 2022Review
- Ferrocenoyl-adenines: substituent effects on regioselective acylation.Beilstein journal of organic chemistry · 2022Article
- Noncovalent CH-π and π-π Interactions in Phosphoramidite Palladium(II) Complexes with Strong Conformational Preference.Angewandte Chemie (International ed. in English) · 2021Article
- A quantitative metric for organic radical stability and persistence using thermodynamic and kinetic features.Chemical science · 2021Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of catalytic enantioselective methods is routinely carried out using easily accessible and prototypical substrates. This approach to reaction development often yields asymmetric methods that perform poorly using substrates that are sterically or electronically dissimilar to those used during the reaction optimization campaign. Consequently, expanding the scope of previously optimized catalytic asymmetric reactions to include more challenging substrates is decidedly nontrivial. Here, we address this challenge through the development of a systematic workflow to broaden the applicability and reliability of asymmetric conjugate additions to substrates conventionally regarded as sterically and electronically demanding. The copper-catalyzed asymmetric conjugate addition of alkylzirconium nucleophiles to form tertiary centers, although successful for linear alkyl chains, fails for more sterically demanding linear α,β-unsaturated ketones. Key to adapting this method to obtain high enantioselectivity was the synthesis of modified phosphoramidite ligands, designed using quantitative structure-selectivity relationships (QSSRs). Iterative rounds of model construction and ligand synthesis were executed in parallel to evaluate the performance of 20 chiral ligands. The copper-catalyzed asymmetric addition is now more broadly applicable, even tolerating linear enones bearing
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.